For those who sync databases across two Macs on iCloud: what’s it like?

I’m going to start a PhD program in the fall and am very much building my Mac setup around DT3. I have fairly large databases on my Mac Mini at the moment.

I’ve been mulling over whether to invest in a powerful laptop, which I’d dock when used at home, versus a Mac Mini + entry-level laptop.

The deciding factor for me is whether DT3 and iCloud sync quickly and reliably between two machines.

If there’s anyone out there with a similar setup reading this, I’d love to hear about your experiences.

Searching for iCloud and sync here should tell you a lot.

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Yes, but I cant tell if such cases are the exception or the rule.

Can you live with exceptional outages of the sync service, possibly at the worst possible moment? If yes, iCloud might be for you.

Whether it’s reliably unreliable is a question nobody here can answer – different users make different experiences at different times and in different locations. There’s no monitoring service for DT’s iCloud sync that could provide solid statistical data.


Fair enough. What’s a better sync service for DT3?

The first question you need to ask yourself is, “Do I need a remote sync option?”. If you have a colleague, assistant, significant other, etc. that needs frequent updates to synced data, then perhaps you do. Otherwise, a local sync is the advocated approach.

The deciding factor for me is whether DT3 and iCloud sync quickly and reliably between two machines.

Legacy is currently more reliable than CloudKit. But again, just having a cloud account does not make it the default or optimal solution here.

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iCloud sync is working well for me (Mac Mini and iPad)
An alternative is direct device<>device via Bonjour

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Most of my DT3 experience in research has involved a combo of MacPro, MacBook (Pro and Air), and iPad. With much help from this forum (often fixing sync issues that I created as a novice), here are a few of my opinions/prefs in no particular order.

  • Store all your databases on a device that will snapshot backup (I use Time Machine and Backblaze and have recovered data from both)
  • Use Bonjour sync to that device that is backing up from the device you take on the road to school/office
  • Follow BLUEFROG’s advice on Shallow Sync DEVONtechnologies | How to Use Shallow Sync to maintain a mobile minimalist database
  • Use DT3 (Hazel too) rules to do the work you can automate on your “host” machine (manipulating, backlinking, tagging, classifying, hookmark links) that will automatically backup
  • Rely as little as possible on the other available sync stores (Dropbox, iCloud, WebDAV) They work, but each adds complexity to troubleshooting your inevitable problems with hardware/software/data. Sync with Bonjour and backup with Time Machine at least.
  • If you are using two MacOS devices (without iOS), Bonjour is simple, fast, well-documented, and supported. (iCloud usually works, but I have lost a lot of productivity during those “other” times.)

I vacillate between liking my MacBookPro and the Air. When my work involved commuting and more travel, the Air won. Now, I am either at my home office or library where I want screenspace on my MacBook Pro. If you use an iPad, it is also an easy addition with Bonjour. I use my iPad to scan docs, annotate with Apple Pencil, present with Keynote, and access frequently used files.

DT3 is a great ecosystem and plays superbly with many other apps. Check out Setapp and when SummerFest/WinterFest deals roll out for great research and writing tools.


FWIW I never had any luck with iCloudKit Syncing. The syncs would never complete. My average database sizes are around 20GB. I also tried iCloud Legacy and Dropbox as well but a similar experience.

So I switched to local-network Bonjour and my life has been much easier.

I only sync the databases I really need on my phone. I could sync them all but the reality is I don’t need to.

How you want to sync will heavily influence your database structure as well. With different databases you can selectively sync the databases you need.

Given I am only syncing my iPhone/iPad to my Mac they are usually never far away from each other for long. When I make changes to documents on my iPhone when out and about, I just sync when I am back in range of my Mac and it does its thing.

Sometimes you need to give it a “kick” to make it start but nothing like the pain of cloud syncing.

I don’t currently have 2 Macs so don’t know how fast Bonjour would be between them, but I expect it would be as good if not faster than my iPhone/iPad syncs.


  • I should add that I select the “Always” option to download all files, not the “On Demand” option. I now have a large capacity 1TB iPhone so I am not constrained by storage space. I certainly was before when I only had 256GB.
  • All my databases are indexed files, but not all files are in iCloud

For three macOS and two iOS devices, I rely on Bonjour and WebDAV on self-hosted NAS. I also occasionally use Dropbox, probably only to prove it just works. I have no luck with Apple’s cloud services which failed as some others report (when tried) with DEVONthink, and often shows shortcomings with other apps that rely on it.

Life’s to short to bang my head to make Apple’s sync services work as I wish.


I’m glad to have this recent discussion to look at. Dropbox has been driving me AROUND THE BEND since the Ventura upgrade. This board was suuuuuuuper helpful in fixing what at first looked like a DevonThink disaster, and DT has been fine since. But Dropbox has continued to cause a regular stream of other problems–constantly ‘breaking’ and having to be reinstalled with a complicated fresh reinstall, each of my 3 main devices (2 desktops and a laptop) taking turns getting screwed up.

So I’ve been thinking about just switching to iCloud on the chance that the story might be Apple making it hard on all the non-iCloud sync services. But it sounds like iCloud is just as frustrating for people as Dropbox has become for me in the last half year!

Dropbox was alway the app that just worked. And it isn’t any more. So I guess just…live with it? Or is there a good just-the-basics ma’am sync service out there that people are happy with? Uggh I just wanna write on computer A and have it appear on computer B and just, like, work every time. That used to be Dropbox!

A pity you have had so much trouble. I would be surprised if reinstalls would fix anything. And what exactly did you reinstall?

Just curious. What were the symptoms to suggest Dropbox syncing broken?

Tried Bonjour?


The so-called “advanced re-install” involves terminal commands that clear caches, helper tools, library files, etc. The first time I did it was with a Dropbox support person live on chat with me. Now it just feels like old hat :rofl:.

Symptoms weren’t subtle: error messages that rendered all syncing nonfunctional–like, “Dropbox can’t start” or “Dropbox sucks” or “Lol you thought you’d fixed me, didn’t you.” Versions of the error described at this link [edit - link fixed] were probably the most recurrent–my guess is that it all stems from Apple making it harder for cloud competitors to integrate. Thank the lord there has never been corruption (so far as I can tell), just makes it impossible for stuff on computer A to get to and from computers B and C.

I’ve never used Bonjour, no. I’m not sure that had even registered as a possible cloud sync solution for my files more generally, though I know it pops up as part of people’s DevonThink setups. (I’m not so great at the computers…)

Malware is all I can guess. Suspicious error messages. Get help soonest.

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Though I don’t know the details, I have a hunch that syncing with Dropbox does not involve using the Dropbox app. And

Well, it’s not cloud, but local. No internet connection involved, no third-party servers (nor your own, btw). Just plain old direct network connection between two machines. Technically, one is the server (and only one – do not turn on Bonjour on several devices if you want to use it for DT syncing!).


And reread the relevant sections about in the “DEVONthink Manual” after your resolve the malware issue (if that is a real issue … sure looks like it based on what you report).

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I’m not sure that had even registered as a possible cloud sync solution for my files more generally,

Bonjour isn’t a “cloud sync solution”. It’s a direct device-to-device connection that can be used to sync DEVONthink as well as DEVONthink To Go.

Do you actually need a cloud synced method? If not, then a Bonjour sync on your local network is suggested.

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yeah it didn’t used to involve a true app; it just “nestled” in your OS as a utility. but whether it’s dropbox’s fault or apple’s fault, the interface has required more and more baggage over the last couple of years. Pretty frustratin…

thank you! i’m in the middle of trying to connect with drobox upport by email. Good times!

I could probably figure out a workaround, but because one of my main machines is at home and another main machine is at the office, there’s no way to get them to talk to each other except via my laptop as an intermediary, which seems to promise sufficient complication that i will surely mess it up : )